DE2150146C3 - Verfahren zur Herstellung von Flavon-7-oxyessigsäureäthylester - Google Patents
Verfahren zur Herstellung von Flavon-7-oxyessigsäureäthylesterInfo
- Publication number
- DE2150146C3 DE2150146C3 DE2150146A DE2150146A DE2150146C3 DE 2150146 C3 DE2150146 C3 DE 2150146C3 DE 2150146 A DE2150146 A DE 2150146A DE 2150146 A DE2150146 A DE 2150146A DE 2150146 C3 DE2150146 C3 DE 2150146C3
- Authority
- DE
- Germany
- Prior art keywords
- ethyl ester
- acid ethyl
- flavone
- oxyacetic acid
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 22
- 239000002253 acid Substances 0.000 title claims description 11
- 125000004494 ethyl ester group Chemical group 0.000 title claims description 10
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 title claims description 6
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 title claims description 5
- 229930003944 flavone Natural products 0.000 title claims description 5
- 150000002212 flavone derivatives Chemical class 0.000 title claims description 5
- 235000011949 flavones Nutrition 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- SULYEHHGGXARJS-UHFFFAOYSA-N 2',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1O SULYEHHGGXARJS-UHFFFAOYSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- UILPJVPSNHJFIK-UHFFFAOYSA-N p-methoxy-o-hydroxyacetophenone Natural products COC1=CC=C(C(C)=O)C(O)=C1 UILPJVPSNHJFIK-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZVXBAHLOGZCFTP-UHFFFAOYSA-N Efloxate Chemical compound C=1C(OCC(=O)OCC)=CC=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 ZVXBAHLOGZCFTP-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- -1 cyano methoxy Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 5
- 150000008041 alkali metal carbonates Chemical class 0.000 description 5
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- KAMXPMMUXJOXMU-UHFFFAOYSA-N 2-(4-acetyl-3-hydroxyphenoxy)acetonitrile Chemical compound CC(=O)C1=CC=C(OCC#N)C=C1O KAMXPMMUXJOXMU-UHFFFAOYSA-N 0.000 description 4
- MQGPSCMMNJKMHQ-UHFFFAOYSA-N 7-hydroxyflavone Chemical compound C=1C(O)=CC=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 MQGPSCMMNJKMHQ-UHFFFAOYSA-N 0.000 description 4
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- ASZXROZTJZAHHL-UHFFFAOYSA-N 2-[3-hydroxy-4-(3-oxo-3-phenylpropanoyl)phenoxy]acetonitrile Chemical compound OC1=C(C=CC(=C1)OCC#N)C(CC(=O)C1=CC=CC=C1)=O ASZXROZTJZAHHL-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GXVYASBPPVUXGP-UHFFFAOYSA-N ethyl 2-(4-acetyl-3-hydroxyphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(C(C)=O)C(O)=C1 GXVYASBPPVUXGP-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical class [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- HCSDAMGBOVWGEO-UHFFFAOYSA-N 3-oxo-3-phenylpropanal Chemical compound O=CCC(=O)C1=CC=CC=C1 HCSDAMGBOVWGEO-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- CYFGXUMPJHJATF-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OC=1C=C(OCC(=O)OCC)C=CC1C(C)=O Chemical compound C(C1=CC=CC=C1)(=O)OC=1C=C(OCC(=O)OCC)C=CC1C(C)=O CYFGXUMPJHJATF-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ZXLFQGWHCIRDIM-UHFFFAOYSA-N ethyl 3-oxo-2-phenoxybutanoate Chemical compound CCOC(=O)C(C(C)=O)OC1=CC=CC=C1 ZXLFQGWHCIRDIM-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2075571 | 1971-02-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2150146A1 DE2150146A1 (de) | 1972-08-31 |
| DE2150146B2 DE2150146B2 (de) | 1974-01-10 |
| DE2150146C3 true DE2150146C3 (de) | 1974-08-15 |
Family
ID=11171574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2150146A Expired DE2150146C3 (de) | 1971-02-19 | 1971-10-07 | Verfahren zur Herstellung von Flavon-7-oxyessigsäureäthylester |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3812156A (fr) |
| JP (1) | JPS4936718B1 (fr) |
| AT (2) | AT306717B (fr) |
| BE (1) | BE767309A (fr) |
| CH (1) | CH525205A (fr) |
| DE (1) | DE2150146C3 (fr) |
| DK (1) | DK126780B (fr) |
| ES (1) | ES391381A1 (fr) |
| FR (1) | FR2125830A5 (fr) |
| IL (1) | IL36979A0 (fr) |
| NL (1) | NL7109389A (fr) |
| SU (1) | SU404238A3 (fr) |
| ZA (1) | ZA715641B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2281112A1 (fr) * | 1974-08-05 | 1976-03-05 | Lipha | Nouveau medicament choleretique et anti-inflammatoire |
| US4025535A (en) * | 1975-03-24 | 1977-05-24 | Dynapol Corporation | Sulfoalkylated flavanone sweeteners |
| AU8045382A (en) * | 1981-12-14 | 1983-06-23 | Pennwalt Corp. | Chromones |
| EP1218002A4 (fr) | 2000-01-24 | 2004-09-22 | Jozef S Mruk | Utilisation d'acide 8-acetique de flavone dans des interventions vasculaires et cardiovasculaires et en cas de syndromes coronariens aigus |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH358092A (it) * | 1955-11-02 | 1961-11-15 | Recordati Lab Farmacologico S | Procedimento per la preparazione di derivati di idrossicromoni |
| CH375020A (it) * | 1957-05-07 | 1964-02-15 | Recordati Lab Farmacologico S | Procedimento per la preparazione del 7-flavonossiacetato di etile |
| CH367833A (it) * | 1957-08-09 | 1963-03-15 | Recordati Lab Farmacologico S | Procedimento per la sintesi del flavon-7-ossiacetato di etile |
| US3467692A (en) * | 1965-05-12 | 1969-09-16 | Allied Chem | Fluorophenoxy alkyl nitriles |
-
1971
- 1971-05-18 BE BE767309A patent/BE767309A/fr not_active IP Right Cessation
- 1971-05-21 ES ES391381A patent/ES391381A1/es not_active Expired
- 1971-05-26 CH CH769771A patent/CH525205A/fr not_active IP Right Cessation
- 1971-06-03 IL IL36979A patent/IL36979A0/xx unknown
- 1971-06-11 DK DK283971AA patent/DK126780B/da unknown
- 1971-07-05 JP JP46049481A patent/JPS4936718B1/ja active Pending
- 1971-07-07 NL NL7109389A patent/NL7109389A/xx unknown
- 1971-07-12 AT AT604871A patent/AT306717B/de not_active IP Right Cessation
- 1971-07-12 AT AT740972A patent/AT310747B/de not_active IP Right Cessation
- 1971-08-04 FR FR7128621A patent/FR2125830A5/fr not_active Expired
- 1971-08-23 ZA ZA715641A patent/ZA715641B/xx unknown
- 1971-10-07 DE DE2150146A patent/DE2150146C3/de not_active Expired
- 1971-10-21 US US00191479A patent/US3812156A/en not_active Expired - Lifetime
- 1971-11-17 SU SU1715244A patent/SU404238A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| DK126780B (da) | 1973-08-20 |
| DE2150146B2 (de) | 1974-01-10 |
| DE2150146A1 (de) | 1972-08-31 |
| SU404238A3 (fr) | 1973-10-26 |
| ZA715641B (en) | 1972-04-26 |
| US3812156A (en) | 1974-05-21 |
| AT310747B (de) | 1973-10-10 |
| ES391381A1 (es) | 1973-07-01 |
| FR2125830A5 (fr) | 1972-09-29 |
| NL7109389A (fr) | 1972-08-22 |
| CH525205A (fr) | 1972-07-15 |
| AT306717B (de) | 1973-04-25 |
| BE767309A (fr) | 1971-10-18 |
| IL36979A0 (en) | 1971-08-25 |
| JPS4936718B1 (fr) | 1974-10-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |